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(-)-Lobeline

(-)-Lobeline structure

(-)-Lobeline 

structure
  • CAS No:

    90-69-7

  • Formula:

    C22H27NO2

  • Chemical Name:

    (-)-Lobeline

  • Synonyms:

    Ethanone,2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-;Lobeline;Ethanone,2-[6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenyl-,[2R-[2α,6α(S*)]]-;α-Lobeline;2-[(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenylethanone;8,10-Diphenyllobelionol;2-[6-(β-Hydroxyphenethyl)-1-methyl-2-piperidyl]acetophenone;Inflatine;(-)-Lobeline;Lobnico;Lobelin;l-Lobeline;L-Lobeline;(-)-α-Lobeline;NIH 11034;8057-04-3

  • Categories:

    Active Pharmaceutical Ingredients  >  Nervous System Drugs

Description

Crystalline solid; melts at 130°C (266°F);slightly soluble in water, dissolves readily inhot alcohol, ether, chloroform, and benzene.


An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.

(-)-Lobeline Basic Attributes

337.45528

337.46

202-012-3

DTXSID3023219

Characteristics

40.54000

3.61

1.1±0.1 g/cm3

130.5 °C

485.6±15.0 °C at 760 mmHg

247.5±20.4 °C

1.563

Subcutaneous-rat LDL0: 80 mg/kg; peritoneal-mouse LD50: 43.5 mg/kg

Lobelia leaves contain lobeline, and cannot be used as tea; thermal decomposition decomposes toxic nitrogen oxide fumes

D15 -43° (alc)

Safety Information

III

6.1(b)

1544

23/24/25

36/37/39-45

T

The warehouse is low-temperature, ventilated and dry; stored separately from food materials

|Danger|H301+H311+H331 (80.41%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 194 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

highly toxic

Drug Information

Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)|Agents that mimic neural transmission by stimulation of the nicotinic receptors on postganglionic autonomic neurons. Drugs that indirectly augment ganglionic transmission by increasing the release or slowing the breakdown of acetylcholine or by non-nicotinic effects on postganglionic neurons are not included here nor are the nonspecific cholinergic agonists. (See all compounds classified as Ganglionic Stimulants.)|Drugs used for their effects on the respiratory system. (See all compounds classified as Respiratory System Agents.)

Lobeline

(-)-Lobeline Use and Manufacturing

Lobeline is the principal lobelia alkaloid.It occurs in the seeds and herb of Indiantobacco (Lobelia inflata and Lobeliaceae). Itis used as a respiratory stimulant. Its sulfatesalt is used in antismoking tablets.

Computed Properties

Molecular Weight:337.5
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:337.204179104
Monoisotopic Mass:337.204179104
Topological Polar Surface Area:40.5
Heavy Atom Count:25
Complexity:412
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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